Top 10 Times Celebrities Flirted with Each Other

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Top 10 Times Celebrities Flirted with Each Other

VOICE OVER: Phoebe de Jeu WRITTEN BY: Robin Schwartzkopf
Flirting celebrities know how to light up a red carpet. For this list, we'll be looking at memorable interactions between stars, whether that's exchanging suggestive messages over social media or sharing a charged moment on the red carpet. Our countdown includes Drake & Nicki Minaj, Gal Gadot & Chris Pine, Drake & Rihanna, and more!
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Top 10 Times Celebrities Flirted with Each Other


Welcome to MsMojo, and today we’re counting down our picks for the Top 10 Times Celebrities Flirted with Each Other.

For this list, we’ll be looking at memorable interactions between stars, whether that’s exchanging suggestive messages over social media or sharing a charged moment on the red carpet. We won’t be including celebrities who were part of an established relationship at the time of the flirting.

What celebrity flirtation did we leave off the list? Let us know in the comments.

#10: Keke Palmer & Timothée Chalamet



The Met Gala is definitely not the worst time to shoot your shot. In 2021, Keke Palmer interviewed Timothée Chalamet at fashion’s biggest night. Palmer’s charisma as an interviewer had Timothée smiling, while his body language suggested a sheepish infatuation. While giving an answer about his wardrobe, he interrupted himself to remind Palmer that the two met when they were just teenagers. He shouted out her mom and then asked Palmer how she was doing before she got the interview back on track to talk about his outfit. Palmer and Chalamet may not be romantically involved, but at least they’ll always have Teen Vogue.

#9: Drake & Nicki Minaj



These two friends have had a flirtatious relationship for a long time, with ups and downs along the way. As far back as his 2010 debut album “Thank Me Later,” Drake’s admiration for Nicki was documented. On the song “Miss Me,” the Canadian rapped about his love for her, and joked about his hopes that the two would marry. Throughout the 2010s, evidence of the chemistry between Drake and Nicki was found on stage, in interviews, over Instagram Lives, and in more lyrics. They never confirmed a romantic relationship, leaving fans to only speculate about their flirty friendship.

#8: Gal Gadot & Chris Pine



It’s no wonder these two co-stars played a convincing couple — they clearly have chemistry. In an interview to promote “Wonder Woman,” Gal Gadot and Chris Pine shared a number of flirtatious glances and exchanges. The body language evidence was also in full view, as the actors touched each other frequently and high five. At one point, Gadot bit her lip while Pine gave an answer. Their natural chemistry was a highlight of the movie’s press tour for fans. Even though the stars kept their romance onscreen, their easy flirtation sparked more than a few rumors about their relationship.

#7: Jack Harlow & Saweetie



Sometimes it’s best to keep it simple. That was rapper Jack Harlow’s strategy when he introduced himself to Saweetie on the BET Awards red carpet in 2021. Harlow offered his hand to Saweetie, and the two went back and forth. Saweetie asked Harlow why he was shaking, to which Harlow placed his other hand on top of hers. The red carpet may not have been an official meet-cute — Harlow actually appeared on the remix of Saweetie’s song “Tap In” in 2020 — but it did inspire a lot of talk on social media about his flirting techniques.

#6: Kendall Jenner & Harry Styles



While the model and the singer did date for some time - as confirmed by Kendall’s mother - their flirtation came years later. Harry Styles filled in for James Corden as host on “The Late Late Show” in 2019, and one guest on the episode was his ex-girlfriend. During a game of Spill Your Guts, Styles and Jenner traded plenty of prickly questions and suggestive glances. While fans may not have learned what songs Styles wrote about Jenner or which celebrities have slid into her DMs, they did bear witness to the still charged relationship between the two.

#5: Lady Gaga & Bradley Cooper



A flirtation is born. The singer and actor appeared together in the 2018 remake of “A Star is Born” and gave plenty of public displays of their affection for one another throughout the film’s press tour and even during the subsequent awards season. Lady Gaga and Bradley Cooper were never officially an item, but they also never wasted an opportunity to give each other warm praise. Their flirtation reached a peak at the Oscars, when the two performed an intimate rendition of the song “Shallow.” Many audiences were convinced of a real-life love story in addition to the one onscreen, but Lady Gaga set the record straight.

#4: Demi Lovato & Henry Cavill



This was a social media flirtation for the history books. Back in 2018 when Instagram allowed followers to see the liking and following activity on other accounts, fans noticed Demi Lovato had taken an interest in the “Superman” actor. Within 30 seconds, the singer started following Cavill, shared an enticing picture of themselves in lingerie, and liked two of his posts. Cavill later responded to their signals by commenting on one of their non-thirst trap pictures. Lovato’s confidence in deploying their social media flirting campaign quickly gained admiration from fans and followers alike — even if it didn’t result in a romantic ending beyond a polite response.

#3: Keanu Reeves & Sandra Bullock



This one spans decades. The actors co starred in the 1994 action movie “Speed.” Audiences picked up on their chemistry on screen and in interviews at the time, but the two never began dating. Years later, Bullock admitted on “Ellen” that she had had a crush on Reeves. Later, Reeves also went on the show and confirmed he had been interested in her as well. Although separate relationships and missed connections got in the way of this couple materializing, the easy flirtation between the two definitely stood the test of time.

#2: Drake & Rihanna


There’s no better time to declare your love than at the MTV VMAs. In 2016, Drake took advantage of his role as presenter to tell Rihanna — who was receiving the night’s “Video Vanguard” award — exactly how he felt about her. The two had shared a flirtatious year, with the dance-filled “Work” music video coming out a few months before. When Drake went in for a kiss onstage at the VMAs, Rihanna responded with a coy kiss on the cheek. This would not be the last time the rapper shared his feelings while on the mic at an awards show. The next year at the Billboard Music Awards, he took time during an acceptance speech to highlight how beautiful he found Vanessa Hudgens.

#1: Lizzo & Chris Evans


The Internet saw it first. Lizzo confessed to her fans over social media that she had sent a drunken DM to Captain America himself — but the flirtation didn’t end there. The actor sent a response, complete with a kissy face emoji. Later, the musician responded to rumors that she was pregnant with his child. Playing along with the joke, Evans sent her a message saying “my mother will be so happy lol.” The suggestive exchanges between the two were tantalizing for fans, as Lizzo provided a peek behind the celebrity curtain by sharing screenshots of their DMs.
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